Island Paradise

By Highlander JM

Published on Jul 8, 2023

Encounters

Story Name / Genre: "Island Paradise" (Part 14 of 25) -

M/F, F/F & just about everything else _____________________________________________________________

I was proud of Christina because at least for this day, she had put forth a lot of effort in trying to make all the other ladies believe that she was the assistant housekeeper. Christina had helped the real maid, Louisa, at almost every turn thus far today - especially when it came to cleaning. She had even collaborated with Louisa in fixing the 7:00pm dinner for everyone - a delicious seafood buffet.

The terrible rainstorm which had moved in during the early morning hours finally came to a welcome end about an hour or so after dinnertime. In terms of being outside and enjoying the island itself, the day had been ruined because of the rain. All of us had been relegated to staying indoors.

But that wasn't so bad, though. Before she went off to help Louisa with the household duties, Christina had offered me a scintillating blowjob which I still fondly remember. Next, Torrie used a strap-on dildo and absolutely hammered Lisa in their bedroom during a fast-paced, fierce encounter.

There were also other noteworthy events which I watched from the prime comfort of my voyeur room.

Lindsay and Trish originally went to the recreation room to hang out and listen to some music. But as was the case more often than not when two beautiful, bi-sexual women were alone together, things heated up rather quickly.

After some tender kisses, Lindsay and Trish began to feel each other up before getting rid of their clothes. Lindsay provided her lover with some breast worship via her mouth, but then squealed with mad passion as Trish went down on her.

Then, Lindsay started to scream out her encouragement as Trish drilled her pussy with an incredibly long dildo. In mid-stream, the two ladies switched to the "69" position, where Lindsay also used a dildo of her own upon Trish. They pounded each other with the big toys while also using their tongues for good measure, until both experienced orgasms.

A bit later on, Amy and Pamela stepped out of the indoor pool upstairs after a long swim and immediately went to work on each others' bodies. They hugged and kissed each other before Pamela told Amy to take a seat in a lounge chair. She did just that, and was rewarded as Pamela knelt between her spread thighs and began swiping away at her pussy.

Amy's words of passion were a bit obscene, so Pamela decided that she needed some discipline because of it. The stacked blonde brought Amy over her lap and gave her a hard, serious spanking while also using her opposite hand to thrust two fingers in-and-out of her pussy. Amy's nasty words continued until she experienced a powerful orgasm.

Returning the favor, Amy placed Pamela over her own lap and offered her a double-penetration - one finger stuffed deep in her ass with another embedded in her pussy. Amy thrusted both fingers in-and-out at a frenetic pace, before laying Pamela out on the floor in front of her.

Amy used her tongue and went to town on her girlfriend's pussy, while continuing to drill her anus with a finger. Now, it was Pamela's turn to talk nasty. She did just that, courtesy of Amy, who eventually helped her "get off".

Near the end of that encounter, Torrie and Lisa started going at it again. In their bedroom, they shared a very deep and passionate kiss which led to some groping as both stripped off whatever (little) clothing they had on.

Torrie stood up with her thighs spread, and allowed Lisa to finger her from behind. This continued for quite awhile, until Torrie turned and instructed Lisa to lay down across the bed. She did, and then Torrie settled down between her outstretched thighs and began lapping away.

Of particular interest - at least to me as I secretly watched the encounter - was the expression upon Lisa's face. The look said it all. With both eyes rolled into the back of her head, Lisa's expression was full of wanton lust. It was very obvious that the 20-year-old was enjoying herself.

She even became more excited once Torrie started using one of her trusty dildos upon her pussy. Lisa switched positions, getting onto her hands and knees, then screamed out in orgasm as Torrie still hammered her with the dildo.

Wanting to reciprocate, Lisa then pinned Torrie beneath her on the bed and kissed her hard. She licked and sucked on both of Torrie's ample-sized breasts before descending even lower, until she reached the joining of her thighs. Lisa's tongue went into overdrive as she made Torrie burn with desire, eventually bringing her to a swift release.

By night-fall, I had stroked my cock so much while watching the various encounters that it was literally raw. I planned on taking a long shower before heading to bed, knowing I needed a good night's worth of rest.

As I was preparing myself for the shower, there was a knock upon the entrance to my personal suite. I wondered who it was for a quick moment until hearing the words, "Open the door, Jeremy." It was Christina.

After she gave me that wondrous blowjob earlier, the little minx proclaimed that she would be spending the night with me this evening. I had almost forgot about it.

As could be expected, Christina immediately got to the point. She was here for a "much-needed fuck" and would, in fact, get several of them before the night was through.

She threw herself at me, offering me a passionate kiss while literally ripping at my muscle-shirt and shorts. I helped her out of her clothing as well - it was very similar to unwrapping a birthday present.

Now able to paw and play with her lithe, petite body, my hands were in their own version of paradise.

My cock soon joined the mix as Christina dropped to her knees and started with her unique brand of oral worship. She sucked me off until I emptied my creamy load deep in her hungry mouth - and she swallowed every single drop.

Intent on providing her with some oral pleasure, I went to work on Christina's pussy with my lips and tongue. But she wanted no part of that. The 20-year-old demanded that not only I fuck her right now, but I also do it in her ass.

Never one to turn such a request, I applied the proper amount of lubricant to her rectum as Christina gave me explicit instructions to do her ass even harder than I had Lindsay's during the past couple of days.

Not wanting to disappoint her, I jammed my shaft into Christina's rectum and began pounding her immediately. She was loud and raucous while thrashing about in response to my thrusts - which was perfect.

I gave her everything I had in terms of pure effort and desire, and only pulled out after pumping a full, heavy load of sperm deep into the tight confines her bowels.


In the morning upon waking up, I peered outside and found nothing but blue skies and bright sunshine, which brought a smile to my face. The island was still water-logged from the rainstorm yesterday, but at least everyone could venture outdoors today and enjoy themselves in the nice, warm sun.

For breakfast, Louisa whipped all of us up some pancakes, which everyone sank their teeth into and mightily enjoyed. Afterward, Christina helped her clear the breakfast table and wash all of the dishes. She was playing her role well...

As usual, the trio of Pamela, Trish and Torrie went to the exercise room for their morning workout. At the same time, Lisa, Lindsay and Amy all decided to go to the beach for some swimming and surfing. Myself? I went to my suite to do some computer and island management work.

Tomorrow, of course, was Amy's birthday. She would be 27. When we woke up earlier, Christina called a friend of hers on the mainland who specialized in lingerie and exotic outfits. Christina arranged for a wide variety of lingerie - ranging all the way from demure to flirtatious, and classy to trashy, to be delivered to the island later this afternoon. Those outfits were going to be used as presents for Amy's birthday.

The price tag was quite expensive, but I made it clear to Christina that money was not an issue - especially since it would be for Amy's birthday.

What I was really hoping for was that Amy, in exchange for her lingerie gifts, would also provide myself and all of the other ladies a present as well - a sexy "fashion show". I would have to wait until tomorrow for that, though.

Nevertheless, my cock twitched at the mere thought.

After finishing up my daily routine on the computer, I decided to go to the exercise room myself for a workout. Unfortunately, our three resident "fitness babes" - Pamela, Trish and Torrie - were nowhere to be found. They must have just left and ventured elsewhere, I told myself.

Although I was looking forward to pumping some iron with the trio of lusty ladies, I decided to put myself through a rigorous workout anyway - even without them.

After three long hours in the weight room, I felt strong and refreshed. I went back to my personal suite and took a quick shower, before deciding to check up on what all the girls were doing with the help of my trusty voyeur room.


Trish and Pamela were in the second phase of their daily routine as they were down at the tennis court, engaged in yet another friendly match.

I've often had fantasies of beautiful, busty competitors on the tennis court throwing down their rackets and deciding to indulge themselves in the pleasures of the flesh. How would you like to see your two favorite "tennis babes" sexing each other up? Perhaps one could lean over the court's net, while having her pussy worshipped from behind...

But my two favorite "tennis babes" were not professional players - they were Trish and Pamela. One of these days, I wanted to come into the voyeur room and find these two ladies at the tennis court not in a friendly match, but a passionate encounter. THAT would be most interesting...

So, Trish and Pamela were busy with their ongoing rivalry. But what about the other ladies? Christina had taken a break from her "maid duties" as she was at the beach - swimming - alongside Amy, Torrie and Lisa. I could tell that the four ladies were having a wonderful time together.

But the woman who seemed to be enjoying herself more than anyone else right now was Lindsay, who found herself in the room she shared with Trish - alone.

I took my cock out and began stroking immediately upon noticing that Lindsay was sprawled out on her bed - totally nude - with her thighs stretched and knees up, and a pair of fingers buried deep in her pussy. The tender, sweet-as-silk blonde was masturbating!

"Oh wow!" I growled out loud, realizing what good fortune this was for me. I flipped the audio for that room on and listened closely as Lindsay emitted sighs and moans as she pleasured herself with two extended fingers.

I actually had the chance to spy and eavesdrop on one of the most private moments any woman could possibly have (at least most women, that is). There was no one else around for the time being as well, so I felt pretty confident that Lindsay would go to every length to make certain she received the greatest amount of self-induced pleasure possible.

Of course, the thought crossed my mind as to why Lindsay would choose to masturbate when any of the other girls would gladly do it for her themselves. On the other hand, perhaps Lindsay was one of those people who needed to touch herself.

As it was, she was all alone in her room while everyone else was enjoying the outdoors. But make no mistake about it - Lindsay was enjoying her sweet self even more.

I continued stroking my cock as the little vixen now used three fingers on herself. I zoomed the camera in for a much closer look and watched intently as she had her tiny clit trapped between two fingers - stimulating it - while using a third to thrust it between the moist folds of her pussy.

I zoomed the camera in even further, and then nearly blew my newfound load as Lindsay's beautiful, lovable pussy filled the entire television screen.

Taking a wider view of the action, I had starry eyes as Lindsay used her free hand to grope and squeeze one of her firm, little breasts. I listened intently as she continued to let out gentle sighs and moans of utter pleasure.

The tender blonde was a pure sweetheart and there was no denying that. Every time I saw her, this thought crossed my mind. Lindsay was so petite and frail - and along with that sweet face and charming smile and personality, she seemed more like a 15-year-old instead of her actual age, 18.

Upon her arrival on the island less than a week ago, it was easy to tell that Lindsay felt somewhat inferior to all of the other ladies. In a mass of large, swarming breasts (Torrie, Pamela, Trish, Amy, Gianna and now Lisa), Lindsay possessed smallish-sized breasts which were easily dwarfed by everyone else (except Christina, who had not arrived yet).

Lindsay even had a discussion with Trish on the subject, telling her how much she preferred the idea of having bigger breasts. Trish told Lindsay that her body was perfectly fine the way it was - and with her petite frame, it would not look right with bigger breasts. Trish did her best to convince her but at the time, I do not think Lindsay bought the idea.

However, less than a week later, I now had the sense that Lindsay's insecure feelings about her body were fading away. After everyone - myself included - had lusted after her this week, perhaps she was starting to realize what Trish told her was the truth. Her body was perfect the way it was.

There were plenty of men and women in the world who would like nothing more than to get their clutches on her lithe, 95 pound frame. Lindsay was starting to see that now. She did not need overflowing breasts to be noticed.

As for the current situation, I was intent on watching Lindsay pleasure herself as she masturbated on her bed. Now, the blonde was frantically thrusting three fingers in-and-out of her little pussy at warp speed as she moaned and writhed about. Of course, I was busy stroking myself!

It seemed as though Lindsay was very close to an orgasm, so I figured the goddess must have wanted to prolong her delight when she withdrew all three fingers from her pussy.

I continued furiously pumping my cock as Lindsay sat up in her bed and then reached into the drawer beside it, in the night-stand. My eyes grew wide as she pulled out a pair of long, thick dildos. I recognized one of them as being the same dildo Amy had first penetrated Lindsay's ass with a couple of days ago...

The 18-year-old giggled with desire as she brought both dildos to her lips and offered them separate kisses. Then, she inserted them into her mouth - one at a time - and gave each a quick but heated sucking. Her next move was to rub the bulging heads of both toys upon her perky nipples.

Suddenly, Lindsay's sweet ass was directly in line with the camera as she rolled onto her stomach and immediately popped up to her hands and knees. I watched with interested eyes as she retrieved a tube of lubricant from the drawer and spread it over and across one of the dildos.

Still on her hands and knees, Lindsay then moaned with pure lust as she reached between her thighs with the other dildo and inserted it between the moist folds of her pussy. She dropped down to her knees and shoulders, with the side of her face upon the bed, then moaned some more while gently moving the dildo in-and-out of her velvety slit.

The enchanting blonde almost blew my mind, however, with what she decided to do next with the first dildo - the same one which had just been lubricated.

With the other embedded deep in her pussy, Lindsay held it in place with her left hand as she used her right to bring the lubed-up dildo over her hip. I let out a moan of pure lust as Lindsay pointed the head of the big joy-toy at her puckered anus, then pushed forward and popped it inside.

She was double-penetrating her own body with two dildos!

"Oh yeah!" Lindsay breathed as she began using some wrist action, pumping the pleasure tools in-and-out of both her pussy and ass at the same time. Her moans became louder as she started to thrash and writhe about upon the bed, her hips gyrating in a rhythmic fashion. "OH FUCK YEAH!" Soon, she was thrusting both dildos as hard as humanly possible.

Watching Lindsay do this to her body reminded me of Amy. Without Amy's prior help and guidance, of course, Lindsay would definitely not being doing this to herself right now. Amy had awakened a sexual monster within Lindsay over the past week with many of the actions and things she had done to her. Of course, Amy was a slut, and I'm quite sure that she had even suggested this form of masturbation to Lindsay.

Such a sweet and innocent teen-ager surely could not think of double-penetrating herself with two dildos without being suggested to do so... could she?

Whatever the case, I could easily envision that slut Amy doing this to her own body back home in Ohio... on those rare nights when she didn't have a cock (or cocks) to indulge in.

It didn't take too long for Lindsay to bring herself to the edge of orgasm. As she impaled herself with the pair of dildos, she made a lot of noise in the process. The lovely blonde was literally raising the roof with her loud screams, as well as her wild grunts and uncontrollable moans.

Lindsay jammed the big dildo in her anus even deeper and released it, then used that hand to slap and spank her very own ass. My cock then exploded as she let out one final, deafening scream.

With one dildo buried in her rectum while still thrusting the other in-and-out her pussy, Lindsay slapped her own ass some more and then went through a massive, earth-shattering orgasm. It was so intense, in fact, that she soon collapsed onto the bed as her arms and legs went completely limp.

"Oh FUCK!" she breathed after several seconds of silence. "That felt GOOD..."

With both dildos now laying on the bed, along with her, Lindsay slipped a hand between her thighs and gently rubbed her pussy. I had just cum all over myself (yet again), but found that I was already starting to get hard once more.


At least for this moment in time, I was tired of watching the girls do their erotic things. It was time to get in on some of the fun. The voyeur room was a wonderful place, but I had no use for it right now. Lindsay had just brought herself to a powerful orgasm with a pair of massive dildos.

Let's see how she responded to a hard, throbbing cock...


Before leaving my personal suite, I did a quick wash-up and then threw on a new shirt and pair of shorts. The whole process took less than 45 seconds. Then, I made a mad dash for the guest corridor and specifically - Lindsay's room.

Collecting myself while trying to harness my urges, I took a deep breath before knocking on the door. I knew that Lindsay was still in her bed, so I waited a few seconds before opening the door and sticking my head in the room.

Feigning both ignorance and concern, I did my best to hide my burning desire as I saw Lindsay curled up underneath a bed sheet, only her head visible as she looked back at me. "Hi there, sweetheart," I said in my softest tone.

"Oh, Jeremy," Lindsay returned, an uncomfortable look on her face as she sat up. I felt sorry for interrupting her fun... but figured she would better enjoy what I had in mind.

I offered a faint smile and put forth my best acting job. "I just heard some screams come from here," I said, which made her eyes grow big. "Sounded like someone was in trouble. I just wanted to check that you were okay."

"Oh..." she said, a confused expression upon her face for a moment. "Oh... yeah. I'm fine. No problems."

I tilted my head and asked, "Then why the screaming? All of the other girls are outdoors, enjoying themselves." I paused and added, "If that wasn't the case, I'd have thought that you were having sex in here with all that noise."

Lindsay's face turned red as she offered a cautious grin. "Well... maybe I was. Having sex, you know..."

"With who?" I inquired, acting even more ignorant. "No one else is around."

Embarrassment washed over her as her lovely face was now a crimson-red. Nevertheless, she answered, "With myself." Lindsay let the bed sheet fall to her waist as she produced one of the dildos and showed it to me.

"OHHHHH..." I grinned, nodding my head. Now, it was time to make my move. "Would you like to have sex with someone other than yourself?" Her eyes loomed large as I continued, "Someone you finds you incredibly sweet and irresistible?"

She giggled and countered, "And who might that be?"

I openly rubbed the very sizable bulge in my shorts and replied, "I think you know who it is, honey."

Lindsay smiled and motioned for me to come closer...


As I made my way over to the bed, I let my shorts fall to the floor and quickly stepped out of them. My cock bulging and out, in open view, I got onto the bed - on my knees - and closed the distance between myself and Lindsay.

She took hold of my shaft and started pumping it with her hand as I found her sweet lips with my mouth. She whacked me off for a bit as I indulged my tongue upon the tasty recesses of her mouth. At the same time, I cupped both of her small breasts in my hands and eagerly squeezed them.

Lindsay broke the kiss rather quickly, however, telling me she had other ideas. Seated upon the bed as I knelt before her, the 18-year-old leaned over slightly and then slipped the full length of my cock into her hungry mouth.

I moaned in sheer ecstasy as Lindsay's blonde head bobbed back-and-forth upon my erection for several seconds, until she decided to concentrate on its bulging head.

Grasping its thick base with her right hand, Lindsay used her luscious, skilled mouth to greedily suck and slurp upon the head of my cock. All the while, her pretty blue eyes stayed locked upon my face.

Soon, however, she released the base of my cock and offered me some no-hands oral. Lindsay's head bobbed about wildly upon my shaft as she clutched her own breasts while also moaning out her own pleasure. In response, I could do nothing but grunt and growl while running my hands through her silky-long, immaculate hair.

Just being able to watch that pretty face as Lindsay sucked me off was enough to bring me to the edge of orgasm.

I could have emptied my load right there - in her mouth - and I'm certain Lindsay would not have complained. However, I was unsure of how much reserve power was left in my body so I decided it would be best to go straight to the main course.

Moaning loudly, I withdrew my cock from the sweet blonde's mouth and then fisted it with my hand. Lindsay looked up at me with puppy-dog eyes as I told her, "Get on your hands and knees, honey. I want to fuck you."

Lindsay offered me an excited smile before she did what I asked of her. Now on her hands and knees, I moved up behind her and immediately grasped her little hips with both hands. A few seconds later, she roared out with a scream as I buried my erection deep between the moist folds of her pussy.

I joined the vocal circus as well, grunting out my delight as I began to pump myself in-and-out of her at a steady pace. I could not believe how incredibly tight her pussy felt upon my cock - it was as if her hand was gripping it fiercely!

Soon, I increased the speed of my thrusts until I was using all of the strength within my body. 95 pounds is the perfect weight for a woman to be pounded - and Lindsay was the best example of why. She was so incredibly hot!

Lindsay let out as a booming scream as I withdrew my cock from her pussy, only then to jam it deep inside her puckered anus. I grunted uncontrollably for a moment as my body adjusted to the newfound sensations. Then, I caught my breath and began pistoning myself in-and-out of her ass.

I continued the anal assault for about 20 seconds before pulling out and stuffing myself into her pussy once again. "OH FUCK!" she screamed in passionate lust, showing her nasty side. "FUCK! WHAT ARE YOU DOING, JEREMY? OH FUCK YES!"

Instead of answering Lindsay verbally, I began hammering her sweet pussy once again. I held onto her hips with all the strength in my hands and arms while blasting her from behind, in the doggie-style position.

It wasn't too long before I had my cock in her ass again.

And then her pussy. Soon, her ass once more...

The constant, back-and-forth switching action had gotten to us both. I mimicked her own actions from earlier as I offered Lindsay's tender ass a series of hard swats with my right hand. She enjoyed the spanking but soon joined me in screaming out in rapture as we experienced mutual orgasms.

I shoved my cock all the way into her rectum and let myself go. Eyes closed and expression tense, I growled in unspeakable desire as I shot my sperm deep within the confines of Lindsay's bowels.

At the same time, the blonde screamed and moaned out her own satisfaction as the orgasmic juices oozed from her pussy. We rocked together for several seconds, each of us trying to help the other experience the ultimate in orgasm while also wanting to get off ourselves. I think we both succeeded

When it was over, I collapsed on top of Lindsay and let out a long, satisfied sigh. With her petite body trapped beneath me, I kissed the back of Lindsay's neck as my cock was still buried in her ass.

"I love you, sweetheart," were my breathless words.


First, it was Pamela. Then Amy. Now... Lindsay.

I suddenly found myself with another new "favorite" girl.

<<<- End of Part 14 ->>>

---------------------------------------- Find every chapter of this story updated and archived at:

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Reader feedback (HighlanderJM@hotmail.com) is appreciated!

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Next: Chapter 15


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